Determination of the barrier to C-N bond rotation in captopril: Application of reference deconvolution to line‐shape analysis
- 1 September 1990
- journal article
- research article
- Published by Wiley in Magnetic Resonance in Chemistry
- Vol. 28 (9) , 820-823
- https://doi.org/10.1002/mrc.1260280916
Abstract
13C NMR was used to study the cis‐trans isomerization of 1‐[(2S)‐3‐mercapto‐2‐methyl‐1‐oxopropyl]‐L‐proline (captopril) in D2O solution over the temperature range 50–100°C. Measurements of the rate of cis‐trans interconversion were made by line‐shape analysis and saturation transfer techniques. The combined results yielded a value for the activation energy of 89 ± 2 kJ mol−1 (21.3 ± 0.5 kcal mol−1) for the C‐N bond rotation. For line‐shape analysis the experimental data were treated by reference deconvolution, using a small amount of labelled acetonitrile as reference, before processing. It was found that the deconvolution process significantly improved the reliability of the analysis.Keywords
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